Réaction #44631

Équation de réaction

cesium fluoride

dioxane

1-bromo-3,4,5-trifluorobenzene

trans-1-propen-1-ylboronic acid

→

title compound

Rendement 84.1%

1,2,3-trifluoro-5-((E)-propenyl)benzene

Rendement 84.1%

Solvants

water

hexane

water

Conditions de réaction

Traitement

1. 1
   AutreThe resulting reaction solution
2. 2
   Températurecooled to room temperature
3. 3
   AutreThe insoluble matter was removed by filtration
4. 4
   AutreThe organic layer of the filtrate was separated
5. 5
   Lavagewashed with water
6. 6
   AutreThe insoluble matter was removed by filtration again
7. 7
   LavageThe filtrate was washed with water
8. 8
   Séchagewith saturated saline, dried over anhydrous magnesium sulfate
9. 9
   Concentrationconcentrated under reduced pressure
10. 10
    AutreThe residue was purified by silica gel column chromatography (hexane)

Mode opératoire

In nitrogen atmosphere, tetrakistriphenylphosphine palladium(0) (4.66 g) and cesium fluoride (21.4 g) were added to a solution mixture of dioxane (95 mL) and water (5 mL) of 1-bromo-3,4,5-trifluorobenzene (8.5 g) and trans-1-propen-1-ylboronic acid (4.1 g). The resulting reaction solution was stirred at 80° C. for 5 hr and then cooled to room temperature, and hexane and water were added thereto. The insoluble matter was removed by filtration. The organic layer of the filtrate was separated and washed with water. The insoluble matter was removed by filtration again. The filtrate was washed with water and then with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane) to give 5.83 g of the title compound. The physical property values of this compound were as follows:

Source